Elevated levels of free radicals, generated as a consequence of ischemic disease, cause damage to biological tissues and ultimately lead to impaired organ function. Strong experimental evidence suggests that partial outlet obstruction of the urinary bladder, that occurs secondary to benign prostate hyperplasia (enlarged prostate), is an ischemic disease involving free radical tissue damage. Antioxidant agents such as lipoic acid, a water soluble cyclic disulfide, and α-tocopherol (vitamin E), a lipid-soluble phenol, possess significant antioxidant properties and have been shown to limit the oxidative damage associated with this progressive bladder disease. In an effort to exploit the unique antioxidant mechanisms associated with each of these antioxidant agents, we have designed a series of adducts of lipoic acid and α-tocopherol. The first in the series of adducts has been synthesized and evaluated for antioxidant activity. These preliminary data show that adducts of lipoic acid and α-tocopherol have enhanced antioxidant activity relative to lipoic acid or α-tocopherol alone. These compounds represent a potential new class of compounds for limiting the progression of obstructive urinary bladder disease.